The synthesis and resolution of (+/-)-1,5,6-tri-O-benzyl-myo-inositol.
Racemic 1,5,6-tri-O-benzyl-myo-inositol was prepared by five routes and converted into 1,5,6-tri-O-benzyl-2,3-O-isopropylidene-myo-inositol, the camphanates of which were readily separated by chromatography. The absolute configurations of the chiral derivatives were established by their conversion into the known chiral 1,4,5,6-tetra-O-benzyl-myo-inositols. 1D-1,5,6-Tri-O-benzyl-2,3-O-isopropylidene-myo-inositol was converted into 1D-1,3,5,6-tetra-O-benzyl-myo-inositol and thence into 1D-2,4-di-O-methyl-myo-inositol. 1D-1,5,6-Tri-O-benzyl-myo-inositol was converted into 1D-1,2,5,6-tetra-O-benzyl-myo-inositol, the diacetate of which is a chiral analogue of "thermosalient crystals". The potential of the above compounds for the synthesis of natural products is surveyed.
Desai
T
T
Laboratory of Lipid and General Chemistry, National Institute for Medical Research, London, Great Britain.
Fernandez-Mayoralas
A
A
Gigg
J
J
Gigg
R
R
Payne
S
S
D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D001593:Benzyl Compounds; C067059:1,5,6-tri-O-benzylmyoinositol; D007294:Inositol